CA2976981A1 - Procede chimique de preparation de derives de pyrimidine et de leurs intermediaires - Google Patents

Procede chimique de preparation de derives de pyrimidine et de leurs intermediaires Download PDF

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Publication number
CA2976981A1
CA2976981A1 CA2976981A CA2976981A CA2976981A1 CA 2976981 A1 CA2976981 A1 CA 2976981A1 CA 2976981 A CA2976981 A CA 2976981A CA 2976981 A CA2976981 A CA 2976981A CA 2976981 A1 CA2976981 A1 CA 2976981A1
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CA
Canada
Prior art keywords
compound
formula
preparing
salt
catalyst
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA2976981A
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English (en)
Inventor
Tobias Kapferer
Baoqing Gong
Mark Clinton DAVIS
Xuchun ZHENG
Denis Har
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Novartis AG
Original Assignee
Novartis AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novartis AG filed Critical Novartis AG
Publication of CA2976981A1 publication Critical patent/CA2976981A1/fr
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

La présente invention concerne un procédé de synthèse de 5-chloro-N2-(2-isopropoxy-5-méthyl-4-(pipéridin-4-yl) phényl)-N4-[2-(propane-2-sulfonyl)-phényl]-pyrimidine -2,4-diamine (ceritinib) et/ou des intermédiaires de ceux-ci, leur utilisation en tant que produits pharmaceutiques et compositions pharmaceutiques et l'utilisation des intermédiaires pour la préparation de ceritinib.
CA2976981A 2015-03-04 2015-03-04 Procede chimique de preparation de derives de pyrimidine et de leurs intermediaires Abandoned CA2976981A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2015/073647 WO2016138648A1 (fr) 2015-03-04 2015-03-04 Procédé chimique de préparation de dérivés de pyrimidine et de leurs intermédiaires

Publications (1)

Publication Number Publication Date
CA2976981A1 true CA2976981A1 (fr) 2016-09-09

Family

ID=56849047

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2976981A Abandoned CA2976981A1 (fr) 2015-03-04 2015-03-04 Procede chimique de preparation de derives de pyrimidine et de leurs intermediaires

Country Status (11)

Country Link
US (1) US20180057457A1 (fr)
EP (1) EP3265455B1 (fr)
JP (1) JP2018508524A (fr)
KR (1) KR20170122807A (fr)
CN (1) CN107531672A (fr)
AU (2) AU2015385326B2 (fr)
BR (1) BR112017017887A2 (fr)
CA (1) CA2976981A1 (fr)
MX (1) MX377139B (fr)
RU (1) RU2703300C2 (fr)
WO (1) WO2016138648A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104803908A (zh) * 2015-03-26 2015-07-29 药源药物化学（上海）有限公司 2-异丙氧基-5-甲基-4-(4-哌啶基)苯胺二盐酸盐的水合物、其制备方法及用途
CN108707120A (zh) * 2018-06-27 2018-10-26 苏州市贝克生物科技有限公司 一种色瑞替尼中间体的合成方法
CN111410649B (zh) * 2019-01-04 2022-09-02 南京海润医药有限公司 一种塞瑞替尼的制备方法
CN109796457B (zh) * 2019-03-28 2020-03-06 苏州国匡医药科技有限公司 一种2-(3-(氮杂环丁烷-3-基)哌啶-1-基)乙基-1-醇的制备方法及其应用
CN111560179A (zh) * 2020-04-01 2020-08-21 德鹿新材料技术(上海)有限公司 一种水性无机相变储能节能涂料及制备方法
GB202007594D0 (en) * 2020-05-21 2020-07-08 Syngenta Crop Protection Ag Chemical process
WO2024172156A1 (fr) * 2023-02-16 2024-08-22 国立大学法人東海国立大学機構 Composé ayant une activité de type brassinostéroïde
CN118146138B (zh) * 2024-02-05 2024-11-05 广州安岩仁医药科技有限公司 一种2-异丙氧基-5-甲基-4-(哌啶-4-基)苯胺盐酸盐的制备方法和应用

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2400477C2 (ru) * 2003-03-14 2010-09-27 Новартис Аг 2,4-ди(фениламино)пиримидины, применимые при лечении неопластических заболеваний, воспалительных нарушений и нарушений иммунной системы
GB0419161D0 (en) * 2004-08-27 2004-09-29 Novartis Ag Organic compounds
GEP20156282B (en) * 2006-12-08 2015-05-11 Irm Llc Compounds and compositions as protein kinase inhibitors
DK2091918T3 (en) 2006-12-08 2014-12-01 Irm Llc Compounds and Compositions as Protein Kinase Inhibitors
WO2009032703A1 (fr) * 2007-08-28 2009-03-12 Irm Llc Composés et compositions inhibiteurs de kinase
CN104109149B (zh) * 2013-04-22 2018-09-28 苏州泽璟生物制药有限公司 氘代的二氨基嘧啶化合物以及包含该化合物的药物组合物
CN104672214B (zh) * 2013-12-03 2019-04-12 上海翰森生物医药科技有限公司 具有alk抑制活性的化合物及其制备与用途
EP3150592B1 (fr) * 2014-05-30 2023-08-30 Shanghai Emerald Wellcares Pharmaceutical Co., LTD Inhibiteur de la kinase alk, son procédé de préparation et son utilisation
CN105272921A (zh) * 2014-06-09 2016-01-27 江苏奥赛康药业股份有限公司 一种制备Ceritinib的方法及其中间体化合物
CN103992262B (zh) * 2014-06-12 2015-11-11 苏州明锐医药科技有限公司 塞瑞替尼及其中间体的制备方法
CN104356050B (zh) 2014-09-30 2017-02-22 常州市勇毅生物药业有限公司 一种色瑞替尼中间体的制备方法
CN104356112B (zh) * 2014-10-30 2017-03-15 南京奇可药业有限公司 一种色瑞替尼的制备方法
CN105646333A (zh) * 2014-11-13 2016-06-08 奥浦顿（上海）医药科技有限公司 色瑞替尼中间体及其制备方法和应用

Also Published As

Publication number Publication date
BR112017017887A2 (pt) 2018-04-10
RU2703300C2 (ru) 2019-10-16
EP3265455A4 (fr) 2019-02-06
WO2016138648A1 (fr) 2016-09-09
AU2015385326A1 (en) 2017-08-31
EP3265455B1 (fr) 2020-07-15
MX2017011330A (es) 2017-12-07
RU2017133858A (ru) 2019-04-08
KR20170122807A (ko) 2017-11-06
AU2019202552B2 (en) 2020-10-29
CN107531672A (zh) 2018-01-02
MX377139B (es) 2025-03-07
RU2017133858A3 (fr) 2019-04-08
JP2018508524A (ja) 2018-03-29
AU2015385326B2 (en) 2019-04-18
AU2019202552A1 (en) 2019-05-02
EP3265455A1 (fr) 2018-01-10
US20180057457A1 (en) 2018-03-01

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